Atroposelective Access to 1,3-Oxazepine-Containing Bridged Biaryls via Carbene-Catalyzed Desymmetrization of Imines.
Atropisomerism
Bridged Biaryls
N-Heterocyclic Carbenes
Organocatalysis
Umpolung
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
02 01 2023
02 01 2023
Historique:
received:
13
08
2022
pubmed:
11
9
2022
medline:
31
12
2022
entrez:
10
9
2022
Statut:
ppublish
Résumé
We disclose herein an atroposelective synthesis of novel bridged biaryls containing medium-sized rings via N-heterocyclic carbene organocatalysis. The reaction starts with addition of the carbene catalyst to the aminophenol-derived aldimine substrate. Subsequent oxidation and intramolecular desymmetrization lead to the formation of 1,3-oxazepine-containing bridged biaryls in good yields and excellent enantioselectivities. These novel bridged biaryl products can be readily transformed into chiral phosphite ligands. Preliminary density function theory calculations suggest that the origin of enantioselectivity arises from the more favorable frontier molecular orbital interactions in the transition state leading to the major product.
Identifiants
pubmed: 36087019
doi: 10.1002/anie.202211977
doi:
Substances chimiques
Imines
0
carbene
2465-56-7
Oxazepines
0
Methane
OP0UW79H66
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202211977Informations de copyright
© 2022 Wiley-VCH GmbH.
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